Hmdb loader

Showing metabocard for Isovaleric acid (HMDB0000718)

Jump To Section:
IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
enzymes (1) Show 1 protein
Show more...Show more...Show more...Show more...Show more...Show more...
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:15:06 UTC
HMDB IDHMDB0000718
Secondary Accession Numbers
  • HMDB00718
Metabolite Identification
Common NameIsovaleric acid
DescriptionIsovaleric acid, is a natural fatty acid found in a wide variety of plants and essential oils. Isovaleric acid is clear colorless liquid that is sparingly soluble in water, but well soluble in most common organic solvents. It has been suggested that isovaleric acid from pilot whales, a species frequently consumed in the Faroe Islands, may be the unusual dietary factor in prolonged gestation in the population of the Faroe Islands. Previous studies suggested that was due to the high intake of n-3 polyunsaturated fatty acids has been, but fatty acid data for eicosapentaenoic acid (EPA) and docosahexanoic acid (DHA) in blood lipids of Faroese and Norwegians was reviewed in terms of the type of fish eaten (mostly lean white fish with DHA much greater than EPA); the popular lean fish, thus, probably provides too little EPA to produce a marked effect on human biochemistry (PMID 2646392 ). Isovaleric acid is found to be associated with isovaleric acidemia, which is an inborn error of metabolism.
Structure
Thumb
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0000718 (Isovaleric acid)

  Mrv1652309272007312D          

  7  6  0  0  0  0            999 V2000
   -1.5400   -0.0116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2546   -0.4241    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5400    0.8134    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8256   -0.4241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1110   -0.0116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1110    0.8134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6034   -0.4241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  1  3  2  0  0  0  0
  2  1  1  0  0  0  0
M  END
Download

3D MOL for HMDB0000718 (Isovaleric acid)

HMDB0000718
     RDKit          3D
Isovaleric acid
 17 16  0  0  0  0  0  0  0  0999 V2000
   -1.1041   -1.0778    0.3055 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2871    0.1879    0.4232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2598    1.3389    0.2805 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7204    0.3330   -0.6970 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6203   -0.8243   -0.6290 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2697   -1.8835   -1.1694 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8261   -0.7437    0.0167 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4639   -1.9728    0.3877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7521   -1.0593   -0.5984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8195   -1.0444    1.1762 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2059    0.1713    1.4212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0747    1.0227   -0.4193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6858    1.5468    1.2755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7843    2.2247   -0.1557 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3232    1.2553   -0.4826 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1875    0.4245   -1.6595 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0782    0.1007    0.5245 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  1  8  1  0
  1  9  1  0
  1 10  1  0
  2 11  1  0
  3 12  1  0
  3 13  1  0
  3 14  1  0
  4 15  1  0
  4 16  1  0
  7 17  1  0
M  END
Download

3D SDF for HMDB0000718 (Isovaleric acid)

  Mrv1652309272007312D          

  7  6  0  0  0  0            999 V2000
   -1.5400   -0.0116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2546   -0.4241    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5400    0.8134    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8256   -0.4241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1110   -0.0116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1110    0.8134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6034   -0.4241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  1  3  2  0  0  0  0
  2  1  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000718

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)CC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C5H10O2/c1-4(2)3-5(6)7/h4H,3H2,1-2H3,(H,6,7)

> <INCHI_KEY>
GWYFCOCPABKNJV-UHFFFAOYSA-N

> <FORMULA>
C5H10O2

> <MOLECULAR_WEIGHT>
102.1317

> <EXACT_MASS>
102.068079564

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
17

> <JCHEM_AVERAGE_POLARIZABILITY>
10.986666365215886

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-methylbutanoic acid

> <ALOGPS_LOGP>
1.26

> <JCHEM_LOGP>
1.208777894

> <ALOGPS_LOGS>
-0.20

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.01023295557517

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
26.4202

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.49e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
isovaleric acid

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0000718 (Isovaleric acid)

HMDB0000718
     RDKit          3D
Isovaleric acid
 17 16  0  0  0  0  0  0  0  0999 V2000
   -1.1041   -1.0778    0.3055 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2871    0.1879    0.4232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2598    1.3389    0.2805 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7204    0.3330   -0.6970 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6203   -0.8243   -0.6290 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2697   -1.8835   -1.1694 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8261   -0.7437    0.0167 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4639   -1.9728    0.3877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7521   -1.0593   -0.5984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8195   -1.0444    1.1762 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2059    0.1713    1.4212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0747    1.0227   -0.4193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6858    1.5468    1.2755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7843    2.2247   -0.1557 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3232    1.2553   -0.4826 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1875    0.4245   -1.6595 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0782    0.1007    0.5245 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  1  8  1  0
  1  9  1  0
  1 10  1  0
  2 11  1  0
  3 12  1  0
  3 13  1  0
  3 14  1  0
  4 15  1  0
  4 16  1  0
  7 17  1  0
M  END
Download

PDB for HMDB0000718 (Isovaleric acid)

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  C   UNK     0      -2.875  -0.022   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -4.209  -0.792   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      -2.875   1.518   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -1.541  -0.792   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.207  -0.022   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.207   1.518   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.126  -0.792   0.000  0.00  0.00           C+0
CONECT    1    4    3    2                                                  
CONECT    2    1                                                            
CONECT    3    1                                                            
CONECT    4    1    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5                                                            
MASTER        0    0    0    0    0    0    0    0    7    0   12    0
END
Download

3D PDB for HMDB0000718 (Isovaleric acid)

COMPND    HMDB0000718
HETATM    1  C1  UNL     1      -1.104  -1.078   0.305  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.287   0.188   0.423  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.260   1.339   0.281  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.720   0.333  -0.697  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.620  -0.824  -0.629  1.00  0.00           C  
HETATM    6  O1  UNL     1       1.270  -1.883  -1.169  1.00  0.00           O  
HETATM    7  O2  UNL     1       2.826  -0.744   0.017  1.00  0.00           O  
HETATM    8  H1  UNL     1      -0.464  -1.973   0.388  1.00  0.00           H  
HETATM    9  H2  UNL     1      -1.752  -1.059  -0.598  1.00  0.00           H  
HETATM   10  H3  UNL     1      -1.819  -1.044   1.176  1.00  0.00           H  
HETATM   11  H4  UNL     1       0.206   0.171   1.421  1.00  0.00           H  
HETATM   12  H5  UNL     1      -2.075   1.023  -0.419  1.00  0.00           H  
HETATM   13  H6  UNL     1      -1.686   1.547   1.276  1.00  0.00           H  
HETATM   14  H7  UNL     1      -0.784   2.225  -0.156  1.00  0.00           H  
HETATM   15  H8  UNL     1       1.323   1.255  -0.483  1.00  0.00           H  
HETATM   16  H9  UNL     1       0.187   0.424  -1.660  1.00  0.00           H  
HETATM   17  H10 UNL     1       3.078   0.101   0.525  1.00  0.00           H  
CONECT    1    2    8    9   10
CONECT    2    3    4   11
CONECT    3   12   13   14
CONECT    4    5   15   16
CONECT    5    6    6    7
CONECT    7   17
END
Download

SMILES for HMDB0000718 (Isovaleric acid)

CC(C)CC(O)=O
Download

INCHI for HMDB0000718 (Isovaleric acid)

InChI=1S/C5H10O2/c1-4(2)3-5(6)7/h4H,3H2,1-2H3,(H,6,7)
Download
View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
Chemical FormulaC5H10O2
Average Molecular Weight102.1317
Monoisotopic Molecular Weight102.068079564
IUPAC Name3-methylbutanoic acid
Traditional Nameisovaleric acid
CAS Registry Number503-74-2
SMILES
CC(C)CC(O)=O
InChI Identifier
InChI=1S/C5H10O2/c1-4(2)3-5(6)7/h4H,3H2,1-2H3,(H,6,7)
InChI KeyGWYFCOCPABKNJV-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as methyl-branched fatty acids. These are fatty acids with an acyl chain that has a methyl branch. Usually, they are saturated and contain only one or more methyl group. However, branches other than methyl may be present.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentMethyl-branched fatty acids
Alternative Parents
Substituents
  • Methyl-branched fatty acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect
Health effectOrganoleptic effect
Disposition
Biological locationRoute of exposureSource
Process
Naturally occurring process
Role
Industrial applicationBiological role
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-29.3 °CNot Available
Boiling Point175.00 to 177.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility40.7 mg/mLNot Available
LogP1.16HANSCH,C ET AL. (1995)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Saliva
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Abnormal Concentrations
Associated Disorders and Diseases
Disease References
Isovaleric acidemia
  1. Krieger I, Tanaka K: Therapeutic effects of glycine in isovaleric acidemia. Pediatr Res. 1976 Jan;10(1):25-9. [PubMed:1246461 ]
Ulcerative colitis
  1. Garner CE, Smith S, de Lacy Costello B, White P, Spencer R, Probert CS, Ratcliffe NM: Volatile organic compounds from feces and their potential for diagnosis of gastrointestinal disease. FASEB J. 2007 Jun;21(8):1675-88. Epub 2007 Feb 21. [PubMed:17314143 ]
  2. Le Gall G, Noor SO, Ridgway K, Scovell L, Jamieson C, Johnson IT, Colquhoun IJ, Kemsley EK, Narbad A: Metabolomics of fecal extracts detects altered metabolic activity of gut microbiota in ulcerative colitis and irritable bowel syndrome. J Proteome Res. 2011 Sep 2;10(9):4208-18. doi: 10.1021/pr2003598. Epub 2011 Aug 8. [PubMed:21761941 ]
  3. Walton C, Fowler DP, Turner C, Jia W, Whitehead RN, Griffiths L, Dawson C, Waring RH, Ramsden DB, Cole JA, Cauchi M, Bessant C, Hunter JO: Analysis of volatile organic compounds of bacterial origin in chronic gastrointestinal diseases. Inflamm Bowel Dis. 2013 Sep;19(10):2069-78. doi: 10.1097/MIB.0b013e31829a91f6. [PubMed:23867873 ]
  4. De Preter V, Machiels K, Joossens M, Arijs I, Matthys C, Vermeire S, Rutgeerts P, Verbeke K: Faecal metabolite profiling identifies medium-chain fatty acids as discriminating compounds in IBD. Gut. 2015 Mar;64(3):447-58. doi: 10.1136/gutjnl-2013-306423. Epub 2014 May 8. [PubMed:24811995 ]
  5. Ahmed I, Greenwood R, Costello B, Ratcliffe N, Probert CS: Investigation of faecal volatile organic metabolites as novel diagnostic biomarkers in inflammatory bowel disease. Aliment Pharmacol Ther. 2016 Mar;43(5):596-611. doi: 10.1111/apt.13522. Epub 2016 Jan 25. [PubMed:26806034 ]
Irritable bowel syndrome
  1. Le Gall G, Noor SO, Ridgway K, Scovell L, Jamieson C, Johnson IT, Colquhoun IJ, Kemsley EK, Narbad A: Metabolomics of fecal extracts detects altered metabolic activity of gut microbiota in ulcerative colitis and irritable bowel syndrome. J Proteome Res. 2011 Sep 2;10(9):4208-18. doi: 10.1021/pr2003598. Epub 2011 Aug 8. [PubMed:21761941 ]
  2. Walton C, Fowler DP, Turner C, Jia W, Whitehead RN, Griffiths L, Dawson C, Waring RH, Ramsden DB, Cole JA, Cauchi M, Bessant C, Hunter JO: Analysis of volatile organic compounds of bacterial origin in chronic gastrointestinal diseases. Inflamm Bowel Dis. 2013 Sep;19(10):2069-78. doi: 10.1097/MIB.0b013e31829a91f6. [PubMed:23867873 ]
Nonalcoholic fatty liver disease
  1. Raman M, Ahmed I, Gillevet PM, Probert CS, Ratcliffe NM, Smith S, Greenwood R, Sikaroodi M, Lam V, Crotty P, Bailey J, Myers RP, Rioux KP: Fecal microbiome and volatile organic compound metabolome in obese humans with nonalcoholic fatty liver disease. Clin Gastroenterol Hepatol. 2013 Jul;11(7):868-75.e1-3. doi: 10.1016/j.cgh.2013.02.015. Epub 2013 Feb 27. [PubMed:23454028 ]
Colorectal cancer
  1. Weir TL, Manter DK, Sheflin AM, Barnett BA, Heuberger AL, Ryan EP: Stool microbiome and metabolome differences between colorectal cancer patients and healthy adults. PLoS One. 2013 Aug 6;8(8):e70803. doi: 10.1371/journal.pone.0070803. Print 2013. [PubMed:23940645 ]
  2. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  3. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
  4. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
  5. Wang X, Wang J, Rao B, Deng L: Gut flora profiling and fecal metabolite composition of colorectal cancer patients and healthy individuals. Exp Ther Med. 2017 Jun;13(6):2848-2854. doi: 10.3892/etm.2017.4367. Epub 2017 Apr 20. [PubMed:28587349 ]
Celiac disease
  1. Di Cagno R, De Angelis M, De Pasquale I, Ndagijimana M, Vernocchi P, Ricciuti P, Gagliardi F, Laghi L, Crecchio C, Guerzoni ME, Gobbetti M, Francavilla R: Duodenal and faecal microbiota of celiac children: molecular, phenotype and metabolome characterization. BMC Microbiol. 2011 Oct 4;11:219. doi: 10.1186/1471-2180-11-219. [PubMed:21970810 ]
Crohn's disease
  1. Walton C, Fowler DP, Turner C, Jia W, Whitehead RN, Griffiths L, Dawson C, Waring RH, Ramsden DB, Cole JA, Cauchi M, Bessant C, Hunter JO: Analysis of volatile organic compounds of bacterial origin in chronic gastrointestinal diseases. Inflamm Bowel Dis. 2013 Sep;19(10):2069-78. doi: 10.1097/MIB.0b013e31829a91f6. [PubMed:23867873 ]
  2. De Preter V, Machiels K, Joossens M, Arijs I, Matthys C, Vermeire S, Rutgeerts P, Verbeke K: Faecal metabolite profiling identifies medium-chain fatty acids as discriminating compounds in IBD. Gut. 2015 Mar;64(3):447-58. doi: 10.1136/gutjnl-2013-306423. Epub 2014 May 8. [PubMed:24811995 ]
  3. Ahmed I, Greenwood R, Costello B, Ratcliffe N, Probert CS: Investigation of faecal volatile organic metabolites as novel diagnostic biomarkers in inflammatory bowel disease. Aliment Pharmacol Ther. 2016 Mar;43(5):596-611. doi: 10.1111/apt.13522. Epub 2016 Jan 25. [PubMed:26806034 ]
Autism
  1. De Angelis M, Piccolo M, Vannini L, Siragusa S, De Giacomo A, Serrazzanetti DI, Cristofori F, Guerzoni ME, Gobbetti M, Francavilla R: Fecal microbiota and metabolome of children with autism and pervasive developmental disorder not otherwise specified. PLoS One. 2013 Oct 9;8(10):e76993. doi: 10.1371/journal.pone.0076993. eCollection 2013. [PubMed:24130822 ]
Pervasive developmental disorder not otherwise specified
  1. De Angelis M, Piccolo M, Vannini L, Siragusa S, De Giacomo A, Serrazzanetti DI, Cristofori F, Guerzoni ME, Gobbetti M, Francavilla R: Fecal microbiota and metabolome of children with autism and pervasive developmental disorder not otherwise specified. PLoS One. 2013 Oct 9;8(10):e76993. doi: 10.1371/journal.pone.0076993. eCollection 2013. [PubMed:24130822 ]
Diverticular disease
  1. Tursi A, Mastromarino P, Capobianco D, Elisei W, Miccheli A, Capuani G, Tomassini A, Campagna G, Picchio M, Giorgetti G, Fabiocchi F, Brandimarte G: Assessment of Fecal Microbiota and Fecal Metabolome in Symptomatic Uncomplicated Diverticular Disease of the Colon. J Clin Gastroenterol. 2016 Oct;50 Suppl 1:S9-S12. doi: 10.1097/MCG.0000000000000626. [PubMed:27622378 ]
Attachment loss
  1. Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Periodontal Probing Depth
  1. Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Supragingival Plaque
  1. Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Tooth Decay
  1. Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Eosinophilic esophagitis
  1. Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.
Associated OMIM IDs
DrugBank IDDB03750
Phenol Explorer Compound IDNot Available
FooDB IDFDB001324
KNApSAcK IDC00001189
Chemspider ID10001
KEGG Compound IDC08262
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link3-Methylbutanoic acid
METLIN ID109
PubChem Compound10430
PDB IDNot Available
ChEBI ID28484
Food Biomarker OntologyNot Available
VMH IDISOVAL
MarkerDB IDMDB00000234
Good Scents IDrw1056411
References
Synthesis ReferenceImada, Yukio; Mizuno, Sumiko; Mikawa, Takashi. Manufacture of isovaleric acid and 2-methylbutyric acid. Jpn. Kokai Tokkyo Koho (1986), 3 pp.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Silva MF, Selhorst J, Overmars H, van Gennip AH, Maya M, Wanders RJ, de Almeida IT, Duran M: Characterization of plasma acylcarnitines in patients under valproate monotherapy using ESI-MS/MS. Clin Biochem. 2001 Nov;34(8):635-8. [PubMed:11849623 ]
  2. Hoffmann GF, von Kries R, Klose D, Lindner M, Schulze A, Muntau AC, Roschinger W, Liebl B, Mayatepek E, Roscher AA: Frequencies of inherited organic acidurias and disorders of mitochondrial fatty acid transport and oxidation in Germany. Eur J Pediatr. 2004 Feb;163(2):76-80. Epub 2004 Jan 9. [PubMed:14714182 ]
  3. Arthur K, Hommes FA: Simple isotope dilution assay for propionic acid and isovaleric acid. J Chromatogr B Biomed Appl. 1995 Nov 3;673(1):132-5. [PubMed:8925066 ]
  4. Ara K, Hama M, Akiba S, Koike K, Okisaka K, Hagura T, Kamiya T, Tomita F: Foot odor due to microbial metabolism and its control. Can J Microbiol. 2006 Apr;52(4):357-64. [PubMed:16699586 ]
  5. Ackman RG: Birthweights in the Faroe Islands: possible role of isovaleric acid. J Intern Med. 1989 Feb;225(2):73-5. [PubMed:2646392 ]

Enzymes

Enzyme Details
1. UDP-glucuronosyltransferase 1-1
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
Isovaleric acid → 3,4,5-trihydroxy-6-[(3-methylbutanoyl)oxy]oxane-2-carboxylic aciddetails